


Dress-Up

by euphemology



Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - High School, Anal Fingering, Anal Plug, Anal Sex, Bottom Castiel, Cas is 16, Desperation, Dirty Talk, Dresses, Frottage, M/M, Panty Kink, Plot What Plot/Porn Without Plot, Top Dean, cas in panties, cross-dressing, dean is 20, lil bit of clothed sex in the beginning uwu, minor underage, they're both so desperate
Language: English
Status: Completed
Published: 2014-02-06
Updated: 2014-02-06
Packaged: 2018-01-11 09:09:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,045
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1171281
Author URL: https://archiveofourown.org/users/euphemology/pseuds/euphemology
Summary: <blockquote class="userstuff">
              <p>This is really just the most gratuitous of smuts, with a little bit of plot thrown in. Dean is home from college and he gets to see 16-year-old Castiel for the first time in two years. He’s definitely grown up.</p>
            </blockquote>





	Dress-Up

**Author's Note:**

> This is gratuitous porn from beginning to end. You've been warned.

“Come on, Dean.  _Please_?” Sam whined.

“Sammy, I got better things to do on a Saturday night than watch you and your friend play video games. Why do Mr. and Mrs. Novak even need me to be there with you two anyway?”

In actuality, Dean had absolutely nothing better to do on a Saturday night, and his plans, before Sam had cornered him, had been to sit in front of the computer and watch Dr. Sexy. Maybe masturbate. Life was unpredictable sometimes. As Dean pulled a beer from the fridge and contemplated appeasing Sam for once, he realized he had spaced out and Sam was still talking away.

“-and then Mr. and Mrs. Novak got super mad because they had locked the liquor cabinet, but someone still managed to get in and I’m 100% positive it was Gabriel, but of course he managed to come up with some kind of fake alibi. Anyway, they’re suspicious of all the kids now.  _Even_   _Cas_. So, yeah. He can’t have any friends over without supervision.” Sam finished, obviously very worked up about the idea of Cas being pegged for something that Gabriel “had obviously done.”

“I dunno, Sam. Why do they want  _me_  to watch you guys? I’m a college student. What’s to stop me from letting you guys have a few drinks?” Dean muttered, before taking a sip of his beer.

“They left you pie in the fridge.” Sam said simply.

“Okay, yeah that works.” Dean chugged the rest of his beer and followed Sam out the door. As they walked to the Impala, Dean couldn’t help but ask something that had been steadily prodding at his mind ever since the conversation about the Novaks had started. “So, uh, Cas is doin’ good?”

“Cas is doing  _well_ , Dean. Why?”

“I dunno.” Dean muttered as the car rumbled to life. “I guess I just haven’t seen him around much anymore.”

“You’ve been at school…” Sam trailed off, looking at Dean like he had grown a second head.

“Don’t look at me like that, Sammy. I’m just wondering ‘cause it’s been like two years since I’ve seen the kid.

“Really? That long?”

Sam was looking out the window with a half-smile and a thoughtful look on his face, both of which made Dean feel even more out of his element.

 

\---

 

When they arrived at the Novak’s house Dean’s urge to eat pie was being quickly overridden by nerves and uneasiness. As he followed Sam to the door, every bone in his body was telling him to turn around.  _Turn back_.  _This could be dangerous._

Castiel Novak, the youngest of the family, had been 14 when Sam invited him over the first time. Dean had been a senior and his first thought when seeing fourteen-year-old Castiel had been,  _fuck._  The kid was too pretty for his own good, and Dean was comfortable enough with himself to admit that the occasional guy definitely did it for him. But this was just…not good.  _He’s Sammy’s age._  As if that would help. The night he had first met Cas had ended with an intense jerk off session featuring blue eyes, a toned little stomach, and messy dark hair.

“Sam! Dean!” Mrs. Novak threw the front door open and gestured them in. “It’s so good to see you! Dean, thanks so much for coming over. We don’t want anyone getting into trouble.”

Mrs. Novak was smiling, but Dean didn’t see. He was too busy looking at the figure coming down the stairs, the word  _trouble_  ringing over and over in his mind.  _Fuck._  Dean didn’t think it was possible for Castiel to get  _prettier_ , but  _fuck._  He was wearing a white shirt that had no business being unbuttoned that far, and a pair of absolutely  _obscene_  black pants. They were so  _tight_  on his firm, slender thighs… his  _crotch_ - _Jesus Christ, Winchester, get it together._

“Hello, Dean.” Dean had to bite the inside of his cheek to prevent any unwanted sounds from leaving his mouth when he heard what two years had done to Castiel’s voice.

“H-hey, Cas. How you doin, man?” Dean could hear how strained his voice sounded in his own ears, and Castiel must have noticed because he immediately looked away, a blush appearing on his pretty cheekbones.

“Sam, it’s good to see you. I think we have some food in the kitchen… Do you want to come eat?” Castiel asked earnestly.

 _Of course._  He probably wanted to get away from Dean’s creepy staring. Dean needed to take himself down, like, twenty notches on the scale of sexual frustration.  _Why hadn’t he jerked off this morning?_

“Well, Dean.” Mrs. Novak was grabbing a wallet and rushing out the door. “They’re all yours. Just make sure they don’t get into the liquor okay?”

“Oh, uh, you got it, Mrs. Novak.” Dean stammered with a wave as she hurried out the door to where Mr. Novak was waiting in the car.

Dean looked down at himself. No visible bulge, but the pressure in his pants told him that this was going to be a problem. He shoved the heel of his hand into his crotch and hissed, before deciding that it was probably best to just avoid the whole situation. He went into the living room and switched on the TV, settling into one of the soft couches. He fell asleep.

 

\---

 

It was dark out when he woke up again. The house was quiet, and the lights were off. Dean rubbed his eyes as he adjusted to the darkness. He could faintly make out a figure on the other couch and, upon further inspection, realized it was Sam.

“ _Sam.”_ Dean hissed, shoving at Sam’s shoulder.

He didn’t wake up. Dean sighed and looked around.  _No sign of Cas_. He wandered into the hallway, and through the kitchen, before backtracking to the main staircase. There was a dim glow coming from somewhere, so Dean started up the stairs and made his way to the only room with a light on. The door was half-open, so Dean pushed it the rest of the way.

“Hey, Cas, you in he – Oh my god.”

Castiel spun around, looking completely horrified, which made sense because Dean had walked in on Castiel all dressed up in this… _this fucking dress_. It was one of those new styles with the slit at the waist and Castiel’s pretty skin was showing, his taut little stomach visible between the gap in the fabric. Dean can’t remember ever getting so hard so fast.

“I-I-“ Castiel stammered, glancing around, looking as if he wanted the ground to swallow him whole.

“Holy shit, Cas.” Dean murmured, walking into the room and shutting the door behind him.

Cas snapped his eyes to meet Dean’s when he heard the tone of Dean’s voice.

“D-do you… _like it?_ ” Castiel whispered, turning to face Dean completely so they were standing less than a foot away from each other.

“I fucking  _love_  it. Where’d you get such a pretty dress, Cas?” Dean’s voice was so strained, his cock pushing painfully against the zip of his jeans as he trailed his eyes down to that little slip of skin the dress revealed so nicely.

Castiel let out this incredibly relieved sigh and suddenly, he was shoving Dean down into the nearest chair, straddling him so that his back pressed against Dean’s chest.

“It’s Anna’s dress. I stole it.” He murmured, as if it was not of consequence, and started grinding his ass against the bulge in Dean’s pants. “I’ve always wanted to sit in your lap, Dean.”

Dean moaned, immediately bringing his hands to Cas’ hips, dragging the dress further up his pretty thighs. He was pretty sure he was dreaming because here he was with a lapful of the sexiest boy he’s ever  _seen_ , who, apparently, just so happened to love dressing up and rubbing himself all over Dean’s cock. Cas was panting as he rotated his hips leisurely, but with so much pressure that Dean was already seeing stars.

“Fuck, baby, unh! Feels so good.” Dean muttered before latching his lips onto the curve of Cas’ neck and sucking. Hard.

Cas made a noise halfway between a whimper and a scream and reached back with one hand to hold Dean’s head in place, rocking his hips harder as his breath started coming in short little pants. He was making so much noise, sounded so desperate just grinding against Dean’s lap, that Dean was just  _dying_  with the need to find out what Cas sounded like when he was full of cock.

“Used to – ah – think about this all the time.” Cas breathed. “Always wanted to do this with you. Make myself – mmmh – pretty for you – ah! – Dean!”

Dean groaned and pulled Cas’ hips down harder, meeting each circle of Cas’ hips with thrusts of his own.

“Fuck, Cas, you’re always pretty. So pretty for me.  _Fuck_.” Dean closed his eyes and dropped his head back, the friction of Cas’ ass against his clothed erection too much and not enough at the same time.

Dean grabbed the sides of the dress, pulling it up around Cas’ waist, and almost came in his pants like a teenager when he saw the little, white lace panties that were stretched over the perfect swell of Cas’ ass.

“Oh fuck, baby.  _Look_   _at you_.” Dean stilled Cas’ movements with one hand, using the other to pull Cas’ panties aside and trace a finger over Cas’ rim –

“Oh my  _god_.” Dean’s voice cracked as he whispered. “Cas, are you wearing a  _plug_?”

Cas was squirming, trying to fuck himself onto the finger tracing his rim as he nodded and whimpered helplessly.

“ _Fuck_ ,  _Cas_.”

Cas moaned as Dean continued to trace around the plug, other hand moving to Cas’ waist to stroke at the exposed skin.

“Fuck, baby, you like that?” Dean asked, voice low and strained.

“Mmmm,  _yes, Dean._ ”

Dean lifted the skirt higher so he could admire the stretched rim of Cas’  _fucking perfect_  ass, but suddenly Cas was standing up, carefully removing the plug with a quiet whimper, and grabbing a small packet from his dresser.

“Wanna fuck myself on your fingers, Dean.” Cas whispered as he straddled Dean’s hips again, this time pressing their chests together, “Then I want you to fuck me.”

Dean let out a wounded moan as Cas grabbed one of his hands, ripping open the packet of lube with his teeth to spread it on Dean’s fingers.

“ _Fuck, angel._ ” Dean whispered as he watched Cas lower himself onto his fingers. “That feel good? Two of my fingers inside you?”

“Yes – ah! – Dean!  _Ah!_ Feels better than I  _imagined_.”

Cas clutched at Dean’s shoulders as he lifted his hips to slam himself back down on Dean’s fingers. Dean watched with rapt attention as Cas lifted the dress with one hand, leaning back slightly so Dean could watch his fingers disappear into Cas’ ass.

 _“Fuck.”_  Dean whispered, eyes wide as he watched Cas grind down on his fingers like he was  _dying_  for it. Like he couldn’t get full enough.

“Mmm!  _Yesss_. Fuck is right.” Cas murmured circling his hips on Dean’s fingers one last time before shifting off so he could unzip Dean’s pants.

“Hang on.” Dean breathed, batting Cas’ hand away and grabbing at his hip with one hand. “You wanted to fuck yourself on my fingers. We’re gonna do that for a little longer, okay? Turn around.”

Cas moaned, thrusting his lace-covered cock against Dean’s stomach  _once_ ,  _twice_ , before Dean forced him up and turned him around.

“Alright, baby. Now come sit on my fingers.” Dean whispered, pushing the dress up so he could watch Cas’ hole flutter as he took three of Dean’s fingers in one go.

“Now fuck yourself.” Dean ordered, his voice so strained as he watched the pretty pink rim clench around his fingers.

“Oh, fuck,  _Deannn._ ” Cas whined, as he began to bounce himself on Dean’s fingers.

Dean was so hard. His dick felt like it was going to rip through his jeans any minute. But he couldn’t look away from how perfect Cas looked, desperately riding his fingers, rotating his hips as he tried to force them against his prostate. Dean chuckled and crooked his fingers. Cas screamed and fucked himself harder, the squelching noise of lube making Dean’s dick twitch. He watched as Cas’ ran his own hands over the bare skin of his waist, before they disappeared under the top piece of the dress.

“ _Fuck._ ” Dean murmured. “You playin’ with your nipples, Cas?

“Unnhh,  _yess, Dean.”_

“That’s a good dress huh?” Dean muttered, still amazed he could form complete sentences while watching Cas’ hot little ass surround his fingers over and  _over._

“ _So good._ ” Cas whimpered. “I’m all pretty for you Dean.  _Mmmm_  want you to fuck me. Please fuck m – ah! – me – hnnghh – I  _need it_. Need your cock inside me.”

Dean groaned, slamming his head back against the chair as he rocked his hips up subconsciously.

“Okay, yeah. Okay, baby, we can do that.” Dean was breathless as he drew his fingers from Cas’ ass, lifting him by the hips so they could both stand. 

Dean’s legs were shaking as he followed Cas to the bed, watching the way the blue dress moved with each sway of Cas’ hips.

“On your hands and knees, baby.” Dean rasped, his voice so far gone at this point.

Cas made a needy little sound and obeyed instantly, climbing onto the bed as he eagerly positioned himself for Dean. Dean followed, kneeling behind Cas as he unzipped his jeans, finally freeing his throbbing cock. He ran a hand over Cas’ ass, giving it a light slap, before lifting the skirt of the dress and pulling down Cas’ panties so they stretched between his thighs. Cas’ hole looked wrecked already and Dean had to wrap a hand around the base of his dick to get things under control. He was dripping lube, and gaping from the plug and his thorough fucking of Dean’s fingers. Dean commits the sight to memory because he’s pretty sure this is the only jerk off material he’ll need ever again.

“ _Deaannnn!”_ Cas whined, thrusting his hips back and clenching his ass with a gasp. “ _Please…”_

“I know, baby, hang on.” Dean murmured, spreading the last of the lube over his cock as he closed his eyes and inhaled deeply, trying to relax enough that he wouldn’t come the second he sheathed himself in Cas’ tight ass. He wanted this to  _last_. He grabbed Cas’ hip with one hand, holding him steady as he rubbed the head of his dick over Cas’ hole.

“ _Dean!_   _Please!_ ”

“What do you want, Cas? You have to tell me.”

“Damnit – ah! –  _Please_ , Dean. Want you to fuck me.  _Need you to fuck me._ ”

“Yeah?” Dean teased as he slowly pushed into Cas’ tight heat. “You need me to fuck you?  _God, baby. You’re such a slut for me.”_

Cas went crazy for that, moaning and thrusting his hips to force more of Dean’s cock inside.

“Only yours, Dean. I’m your slut.” Cas whispered when Dean was  _finally_  all the way inside.

“ _Fuck._  That’s right, baby.” Dean hissed as he began to rock his hips slowly, loving the way Cas’ ass looked stretched around his dick. “So fucking desperate for me you’ll take anything I give you.”

“ _Yes yesss – ah! – Dean!”_

Dean began thrusting faster, draping himself over Cas’ back as he ground his hips against his ass. He snaked his hands over the slip of skin at Cas’ waist, fingers slipping underneath the fabric to grab at his nipples, twisting them between his fingers and making Cas cry out.

“Fuck, baby, you’re so good for me.” Dean moaned, lifting himself back up so he could have better leverage as he quickened his thrusts. 

Cas wailed as the change in angle allowed Dean to slam against his prostate.

“Dean,  _f-f-fuck, ah-ah!”_  Cas’ breath was being punched out of him with each hard thrust of Dean’s dick.

The sounds went straight south and Dean felt himself losing his rhythm as the heat in his abdomen grew. His thrusts were losing precision and he quickly put a hand at the back of Cas’ neck and shoved him down into the bed to get a better angle.

“You gonna come for me, Cas?” Dean asked, his voice rough and strained as he looked at Cas sprawled out underneath him just  _taking everything._  “You gonna come all over yourself? Bet you can do it without me even touching your cock, baby. So good for me  _fuck._  Plug in your ass all day, all dressed up for me, just  _waiting_  for me to bend you over the nearest surface and  _fuck_  you until you couldn’t  _stand_.”

“Yes, Dean, please! Ah!” Cas was gasping, ass thrusting back against Dean’s dick.

“ _Fuck, baby.”_  Dean nearly whined, driving his hips even faster so that all Cas was capable of were punched-out gasps and moans. “Gonna do this all the time now. Dress you up, put a nice fake cock in your ass, make you wear it all day until I’m ready to fuck you.”

“Fuck – mmh! Dean! Gonna – oh please - ah! Fuck!  _Fuck! Dean!_ ”

Cas’ back arched as he came and it was fucking  _beautiful_. But Dean didn’t have time to admire it because Cas’ ass was clamping down hard on his dick and driving him over the edge as he groaned, his release hitting him like a punch in the gut. He continued to fuck slowly, in and out, as he came down from his high, his dick still hard since Cas was clenched around him so tight.  As he began to soften, he pulled out, cock giving a valiant twitch when he saw the state of Cas’ hole.

“Mmmm, Dean.” Cas flipped himself over, stretching on the bed with the biggest fucking grin on his face. “Wanna kiss you.”

Dean laughed when he realized they hadn’t even kissed yet and draped himself over Cas as he brought their mouths together. The sex was… well, fucking  _phenomenal_. Dean’s never come so hard in his  _life_. But this? This was perfect too. Cas’ lips so soft, warm, against his, hands carding through his hair… Dean could get used to this.

**Author's Note:**

> Comments mean more panty fics for you guys uwu


End file.
